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锌和铜催化的叔溴代烷与草酸盐的偶联反应,用于构建具有挑战性的 C-O、C-S 和 C-N 键。

Zn- and Cu-Catalyzed Coupling of Tertiary Alkyl Bromides and Oxalates to Forge Challenging C-O, C-S, and C-N Bonds.

机构信息

Center for Supramolecular Chemistry and Catalysis, Department of Chemistry, Shanghai University, 99 Shang-Da Road, Shanghai 200444, China.

出版信息

Org Lett. 2021 Feb 5;23(3):1005-1010. doi: 10.1021/acs.orglett.0c04206. Epub 2021 Jan 14.

Abstract

We describe here the facile construction of sterically hindered tertiary alkyl ethers and thioethers via the Zn(OTf)-catalyzed coupling of alcohols/phenols with unactivated tertiary alkyl bromides and the Cu(OTf)-catalyzed thiolation of unactivated tertiary alkyl oxalates with thiols. The present protocol represents one of the most effective unactivated tertiary C(sp)-heteroatom bond-forming conditions via readily accessible Lewis acid catalysis that is surprisingly less developed.

摘要

我们在这里描述了通过 Zn(OTf)催化的醇/酚与未活化的叔烷基溴的偶联以及 Cu(OTf)催化的未活化的叔烷基草酸酯与硫醇的硫代反应,轻松构建空间位阻的叔烷基醚和硫醚的方法。该方案代表了通过易于获得的路易斯酸催化形成最有效的未活化的叔 C(sp)-杂原子键的条件之一,而这种催化方法的发展却出人意料地较少。

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